Basic information
- CAS
1080-12-2- Standard SMILES
COc1cc(C=CC(C)=O)ccc1O- InChIKey
AFWKBSMFXWNGRE-UHFFFAOYSA-N- Molecular formula
- C11H12O3
- Average molar mass
- 192.21 g/mol
- Monoisotopic mass
- 192.07864424
Overview
vanillylidene acetone has been reported in Fibraurea tinctoria and Curcuma longa with data available.
Names & identifiers
- Preferred name
- 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one
- IUPAC
- 4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
- English name
- Vanillylidenacetone
- Molecular formula
- C11H12O3
- Molecular weight
- 192.21
Names & synonyms
DTXSID2061480dehydrozingerol4-hydroxy-3-methoxybenzalacetoneMethyl-3-methoxy-4-hydroxystyryl ketoneMMHSKRefChem:912190DTXCID20331044-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-oneVanillidene acetoneVanillylidene acetone3-Buten-2-one, 4-(4-hydroxy-3-methoxyphenyl)-, (3E)-SCHEMBL498224
Show more names
DEHYDROZINGERONEferuloylmethaneVANILLYLIDINE ACETONE4-(4-HYDROXY-3-METHOXYPHENYL)BUT-3-EN-2-ONEmhskFEMA 3738vanillalacetoneDehydrogingeroneVanillideneacetone
SCHEMBL2832718SCHEMBL30310276AFWKBSMFXWNGRE-UHFFFAOYSA-NDB-040801NS000214981-(4-Hydroxy-3-methoxyphenyl)-1-buten-3-one4-(4-hydroxy-3-methoxy-phenyl)but-3-en-2-one1-(3'-methoxy-4'-hydroxyphenyl)-1-butene-3-one
Database identifiers
- CAS
1080-12-2- PubChem CID
- 14121
- DTXSID
DTXSID2061480- EC Number
- 214-096-9
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 223
Experimental & physicochemical properties
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Physicochemical properties
- Melting point
- 125 · 125-130 °C
- Boiling point
- 268.19 °C · 268.19°C (rough estimate)
- Density
- 1.1503 · 1.1503 (rough estimate)
- refractive index
- 1.46 · 1.4600 (estimate)
- FEMA
- 3738 · 3738 | VANILLYLIDENE ACETONE
- FLAVIS Number
- 7.046 · 07.046 | Vanillylidene acetone
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml).
- pka
- 9.94 · 9.94±0.31(Predicted)
- form
- solid
- color
- Pale yellow
- Odor
- 100 % · at 100.00 %. sweet powdery vanilla creamy balsam
- Odor Type
- vanilla
- JECFA Number
- 732 · 732
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
- InChI
- 1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+
- InChIKey
- AFWKBSMFXWNGRE-ONEGZZNKSA-N
- SMILES
- COc1cc(\C=C\C(C)=O)ccc1O
- LogP
- 1.4 · 1.40
- CAS DataBase Reference
- 1080 · 1080-12-2(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- VANILLYLIDENE ACETONE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 8 CJX5I27B7 · 8CJX5I27B7
- EPA Substance Registry System
- 3 · 3-Buten-2-one, 4-(4-hydroxy-3-methoxyphenyl)- (1080-12-2)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36/37/39
- WGK Germany
- 3 · 3
- RTECS
- 9960000 · EM9960000
- F
- 10 · 10-23
- TSCA
- TSCA listed
- HS Code
- 29145090 · 29145090
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 intraperitoneal · LD50 intraperitoneal in mouse: 610mg/kg
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Hazard Classes and CategoriesAcute Tox. 4 (50%)
Safety data
- F
- 10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- EM9960000
- hs_code
- 29145090
- Toxicity
- LD50 intraperitoneal in mouse: 610mg/kg
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 26-36/37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Use ClassificationFlavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
DescriptionDehydrozingerone (1080-12-2) is a structural half analog of curcumin (Cat.# 10-1243) and is isolated from ginger rhizomes. Dehydrozingerone displays antioxidant, antibacterial and antifungal properties.1 It has also been shown to possess various antitumor effects2,3 and inhibit growth factor/peroxide-stimulated vascular smooth muscle function4.
UsesVanillylidenacetone is one of ferulic acid derivatives. Studies have shown that vanillyl acetone has a certain inhibitory effect on Amaranthus, barnyardgrass, matang, dogwood and rape, among which the best inhibitory effect is on rape and Amaranthus.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers93 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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Additional notes
DefinitionChEBI: Dehydrozingerone is a hydroxycinnamic acid.
Related reactions
12 records
Compound notes
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